The bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. In this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. The synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers.

Faculty of Forestry and Wood Sciences Department of Forest Protection and Entomology Czech University of Life Sciences 165 21 Prague Czech Republic

Faculty of Forestry and Wood Sciences Extemit K group Czech University of Life Sciences 165 21 Prague Czech Republic

Faculty of Tropical AgriSciences Department of Crop Sciences and Agroforestry Czech University of Life Sciences 165 21 Prague Czech Republic

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Research Group of Infochemicals 166 10 Prague Czech Republic

Mid Sweden University Department of Chemical Engineering SE 851 70 Sundsvall Sweden

See more in PubMed

Mori K. Significance of chirality in pheromone science. Bioorg. Med. Chem. 2007;15:7505–7523. doi: 10.1016/j.bmc.2007.08.040. PubMed DOI

Kindl J, Kalinová B, Červenka M, Jílek M, Valterová I. Male moth songs tempt females to accept mating: The role of acoustic and pheromonal communication in reproductive behaviour of Aphomia sociella. PLoS One. 2011;6:e26476. doi: 10.1371/journal.pone.0026476. PubMed DOI PMC

Kindl J, Jiroš P, Kalinová B, Žáček P, Valterová I. Females of the bumblebee parasite, Aphomia sociella, excite males using a courtship pheromone. J. Chem. Ecol. 2012;38:400–407. doi: 10.1007/s10886-012-0100-3. PubMed DOI

Kunesch G, Zagatti P, Pouvreau A, Cassini R. A fungal metabolite as the male wing gland pheromone of the bumble-bee wax moth. Aphomia-sociella L. Z. Naturforsch. C: Biosci. 1987;42:657–659. doi: 10.1515/znc-1987-0525. DOI

Kalinová B, et al. Composition and electrophysiological activity of constituents identified in male wing gland secretion of the bumblebee parasite Aphomia sociella. J. Nat. Prod. 2009;72:8–13. doi: 10.1021/np800434x. PubMed DOI

Lebedeva KV, Vendilo NV, Ponomarev Vl, Pletnev VA, Mitroshin DB. Identification of pheromone of the greater wax moth Galleria mellonella from different regions of Russia. IOBC WPRS Bull. 2002;25:229–232.

Sasaerila Y, et al. Sex pheromone components of male Tirathaba mundella (Lepidoptera:Pyralidae) Chemoecology. 2003;13:89–93. doi: 10.1007/s00049-003-0233-5. DOI

Hall DR, Cork A, Lester R, Nesbit BF, Zagatti P. Sex pheromones of rice moth, Corcyra cephalonica Staintion II. Identification and role of female pheromone. J. Chem. Ecol. 1987;13:1575–1589. doi: 10.1007/BF00980201. PubMed DOI

Nieberding CM, et al. The male sex pheromone of the butterfly Bicyclus anynana: towards an evolutionary analysis. PLoS One. 2008;3:e2751. doi: 10.1371/journal.pone.0002751. PubMed DOI PMC

Hedenström E, et al. Stereoisomeric analysis of 6,10,14-Trimethylpentadecan-2-ol and the corresponding ketone in wing extracts from African Bicyclus butterfly species. J. Chem. Ecol. 2015;41:44–51. doi: 10.1007/s10886-014-0539-5. PubMed DOI

Eltz T, Hedenström E, Bång J, Wallin EA, Andersson J. (6R,10R)-6,10,14-Trimethylpentadecan-2-one, a dominant and behaviorally active component in male orchid bee fragrances. J. Chem. Ecol. 2010;36:1322–1326. doi: 10.1007/s10886-010-9873-4. PubMed DOI

Ptáček V, Pernová E, Borovec R. The two-queen cascade method as an alternative technique for starting bumble bee (Bombus, Hymenoptera, Apidae) colonies in laboratory (Preliminary study) Pszczel. Zesz. Nauk. 2000;44:305–309.

Farine J-P. The exocrine glands of the male of Eldana saccharina Walker (Lepidoptera, Galleriinae): Intervention in precopulatory behavior. J. Morphol. 1983;178:77–87. doi: 10.1002/jmor.1051780106. PubMed DOI

Bång J, Hedenström E, Anderbrant O. Stereoisomeric separation of derivatized 2-alkanols using gas chromatography-mass spectrometry: sex pheromone precursors found in pine sawfly species. Anal. Lett. 2012;45:1016–1027. doi: 10.1080/00032719.2012.670789. DOI

Nieberding CM, et al. Cracking the olfactory code of a butterfly; the scent of ageing. Ecol. Lett. 2012;15:415–424. doi: 10.1111/j.1461-0248.2012.01748.x. PubMed DOI

Schulz S, Yildizhan S, van Loon JJA. The biosynthesis of hexahydrofarnesylacetone in the butterfly Pieris brassicae. J. Chem. Ecol. 2011;37:360–263. doi: 10.1007/s10886-011-9939-y. PubMed DOI